Your insider's guide to the best things to do, see, and experience in Chicago.
5 MIN READ — Chicago has once again been crowned the Best Big City in the U.S. in the Condé Nast Traveler Readers’ Choice Awards, one of the most prestigious recognitions a destination can receive. This is the ninth consecutive year Chicago has claimed this title, a streak unprecedented in the awards program’s more than 30-year history.
4 MIN READ — Chicago Loop Alliance is announcing programming for the fall season under the campaign, Falling for the Loop, positioning the month of October as a celebration of arts and culture.
As the air cools and leaves begin to change, First Lady invites locals and visitors to experience fall in Chicago from the water. Now through November, guests can enjoy crisp breezes, glowing sunsets, and stunning skyline views aboard a variety of sightseeing and specialty cruises.
5 MIN READ — Crisp air, cozy sweaters, and vibrant colors mean one thing—fall has arrived in Chicago! From festive riverfront celebrations and pumpkin patches to colorful Halloween experiences and seasonal treats, the city is buzzing with ways to soak in the season. This guide is your go-to for the best fall happenings in the Chicago Loop—perfect for family outings, date nights, or a fun day with friends.
5 MIN READ: LUMA8 and the City of Chicago present the 11th Annual Arts in the Dark Halloween Parade—a family-friendly celebration featuring dazzling floats, larger-than-life puppets, and dynamic performances. The parade takes place on Saturday, October 18, from 6–8 p.m. along historic State Street, stepping off at Randolph Street. This event is also part of Chicago Loop Alliance’s Falling for the Loop fall programming.
2 MIN READ – There are many ways you can honor and celebrate Hispanic Heritage Month, which takes place September 15 through October 15. Here are a few ways you can support and uplift Hispanic arts & culture in the Loop!
2 MIN READ: The Christkindlmarket is delighted to announce the return of its cherished holiday tradition for its 29th season at Daley Plaza in Chicago, with new special activations.
2 MIN READ — The City of Chicago has officially approved the 2025 Chicago River Swim (CRS), marking the
first open water swim in the Chicago River in 98 years. Set for Sunday, September 21, 2025, this landmark
event will celebrate the city’s environmental progress and generate critical funds for ALS research and youth
swim education programs.
March 15, 2026
Chicago’s top-rated architecture boat tour, 90 minutes with expert CAC guides, stunning skyline views, open-air seating, and onboard amenities.
March 21, 2026
Explore Chicago’s haunted past on a nighttime river cruise featuring ghost stories, mob history, and eerie secrets of the Windy City.
April 17, 2026
Chicago River & Lake Michigan cruise with skyline views, iconic landmarks, and engaging guides sharing the city’s history and stories.
April 17, 2026
Experience Chicago at night on a 90-minute river and lake cruise, featuring a glittering skyline, cool breezes, and lively, family-friendly commentary.
April 22, 2026
Directed by Andrew Scoville. Co-created by Academy, Grammy, and Tony Award-winning artist David Byrne* and writer Mala Gaonkar, Theater of the Mind is a new theatrical…
July 11, 2026
Cruise Chicago’s waterways with your dog. Pet friendly, scenic, and fun. Available July to October every Saturday and Sunday for pups of all sizes.
September 4, 2026
Experience Jaw-Dropping Magic. Enter through the doors at 50 West Randolph to discover a hidden world where the impossible becomes…
September 5, 2026
Sept 5 - Oct 4, 2026 "The Goodman premieres The 7 Fingers' "The Attic Things I’ve Seen While Lying On…
September 8, 2026
Kokandy Productions’ critically acclaimed revival of the 10-time 2025 Jeff Award–nominated musical JEKYLL & HYDE will make its Broadway In Chicago debut at the Broadway Playhouse…
